Calcium-Catalyzed Bis-hydrothiolation of Unactivated Alkynes Providing Dithioacetals
作者:Martin Hut’ka、Tetsu Tsubogo、Shu̅ Kobayashi
DOI:10.1021/om500442u
日期:2014.10.27
Bis-hydrothiolation of alkynes providing anti-Markovnikov dithioacetals is reported. Lewis-acidic Ca(OSO2C4F9)(2) (Ca(ONf)(2)) was synthesized for the first time and was shown to be an excellent catalyst for the transformation. The reaction is highly selective and has a wide substrate scope. It was revealed that vinyl sulfides were intermediates for this transformation and that Ca(ONf)(2) efficiently catalyzed the unprecedented reactions of unactivated vinyl sulfides with thiols to afford the dithioacetals in good to high yields.
Super electron donor-mediated reductive desulfurization reactions
The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.